Simon played schoolboys football with Cherry Orchard and Shelbourne before joining Leeds United as a trainee in 2004 aged just sixteen. He become a professional two years later and made his debut against Bury in a Football League Trophy match at Elland Road in November 2007 which ended in a 2-1 defeat.

In April 2008 Simon had an unsuccessful trial with Cheltenham Town, and was released from his contract with Leeds a few days later. He returned to Ireland and soon put pen to paper on a deal with Shamrock Rovers, making his Hoops debut in a 1-1 draw at Saint Patrick’s Athletic on 21 July 2008 and going on to make 25 league appearances over the next year and a half.

He was released by Rovers at the end of 2009 but followed ex-teammate Tadhg Purcell to Darlington in January 2010 when he was signed by Steve Staunton. He made his bow in a 3-0 defeat by Crewe Alexandra, and a poor season for the club ended with them being relegated from the Football League as they finished at the foot of League Two.

Madden was released along with 13 other Darlington players and in July 2010 and signed for Ian Foster at Dundalk. He made 15 league appearances over the latter half of 2010 and was ever-present in 2011, also captaining the side as Dundalk finished seventh in the Premier Division.

In January 2012 Simon signed for Declan Devine at Derry City where he made his club debut against Bohemians on the opening night of the 2012 season. He made 28 league appearances that year and also picked up an FAI Cup winners medal as Derry defeated St Patrick's Athletic in the final. In 2013 Simon played all 33 of Derry's league games, scoring once, in the last game as Derry beat Limerick 6-0. Along with numerous man of the match awards, he was named in the RTE Team of the Year as Derry City came fourth in the league.

Simon returned to Shamrock Rovers in November 2013 and played in 32 of the club's thirty-three Premier Division games, scoring once in a 1-0 win over Sligo Rovers, as the Hoops finished in fourth place. And in 2015 Simon was ever-present, playing in all 33 league games as Shamrock Rovers finished third in the Premier Division. He also played in all four of the club's Europa League matches as Rovers went to Norwegian side Odds.

Simon was again ever-present in the Hoops' defence in 2016, making another 33 league appearances. He also played in both of the club's Europa League games against RoPS of Finland and subsequently re-signed with Shamrock Rovers for 2017. Simon was released from Shamrock Rovers at the end of the 2017 campaign having made 194 appearances over two spells with the Hoops.

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